Sodium Carbonate → HCID 60143031, compound

HRID 925508Notes

Reaction equation

HRID 925508 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[CH2:12][N:13]([CH3:28])[C:14](=[O:27])[N:15]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([CH3:26])([CH3:25])[C:23]#[N:24])=[CH:18][CH:17]=4)[C:5]=3[C:4]=2[N:3]=1.[CH3:29][O:30][C:31]1[N:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:29][O:30][C:31]1[N:36]=[CH:35][C:34]([C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][C:6]4[CH2:12][N:13]([CH3:28])[C:14](=[O:27])[N:15]([C:16]5[CH:21]=[CH:20][C:19]([C:22]([CH3:26])([CH3:25])[C:23]#[N:24])=[CH:18][CH:17]=5)[C:5]=4[C:4]=3[N:3]=2)=[CH:33][CH:32]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 90449300HCID 90449300, compound

Product 1

HCID 60143031HCID 60143031, compoundYield 14.4%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

2-(4-(9-chloro-3-methyl-2-oxo-3,4-dihydropyrimido[5,4-c][1,5]naphthyridin-1(2H)-yl)phenyl)-2-methylpropionitrile (700 mg, 1.79 mmol) and 6-methoxy-3-pyridine boronic acid (328 mg, 2.15 mmol) were dissolved in toluene (30 mL) and ethanol (10 mL), to the system added tetrakis(triphenylphosphine) palladium (40 mg) and 2N aqueous sodium carbonate solution (2.7 mL). Refluxed and reacted under nitrogen for 3 h, cooled to room temperature, filtered, the organic layer was concentrated under reduced pressure, dissolved in 50 mL of dichloromethane, washed sequentially with water and saturated brine, and the organic layer was dried over anhydrous sodium sulfate, and concentrated. The resulting solid was subjected to silica gel column chromatography (ethyl acetate:petroleum ether=1:1) to give 120 mg of the product.

Workup

  1. temperatureRefluxed
  2. customreacted under nitrogen for 3 h
  3. filtrationfiltered
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. dissolutiondissolved in 50 mL of dichloromethane
  6. washwashed sequentially with water and saturated brine
  7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cba95120b9a24cc1a42cb260a65eb5cf
Source dataset
uspto-grants-2016_03
Patent number
US09284315B2

Reaction notes

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